Both teams should have:
Optional characters might include (but feel free to suggest others):
William Dean Howells: Editor of The Atlantic, which published some of the “tales.” Howells was a literary kingmaker and arbiter of the dominant literary style of “realism,” so playing Howells allows you to explore the way CC navigated literary culture and the important institution of the “quality” magazines that published serious fiction and lent prestige to writers.
George W. Cable: White “Local Color” writer from the South with liberal sensibility. Friend of CC who advised him on how to navigate the literary marketplace.
Walter Hines Page: Chesnutt’s editor at the Atlantic. This role would really let you get into the nitty-gritty of how CC navigated between his own artistic vision and the realities of readers’ expectations about blackness.
Reviewer: There is a wealth of reviews published in print form and available on the web. You could create a persona (give it a real name!) and weave together some real reviews of the “tales,” emphasizing how reviewing shapes the reception and reading of texts.
“General Reader”: you could “play” a reader, and thematize the pleasures of dialect and “plantation” fiction from the POV of a white reader, or perhaps a more ambivalent response from an African American reader, with a mix of “race pride” and [fill in the blank] about the problematic contours of the genre.
Mark S. suggested playing W. E. B. Du Bois, which would be quite interesting and speculative, especially if you know something about his career. He also mentioned more recent critics, like Eric Sundquist or Joseph McElrath: the later edited much of CCs speeches, letters, and journals, so that would be interesting.